Difference between revisions of "Mauveine"
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[[Image:Mauv2.jpg|thumb|right|Letter from Perkin's son, with a sample of dyed silk]] | [[Image:Mauv2.jpg|thumb|right|Letter from Perkin's son, with a sample of dyed silk]] | ||
| − | '''Mauveine''', also known as '''[[aniline]] [[purple]]''' and '''Perkin's mauve''', was the first synthetic [[organic chemistry|organic]] [[dye]].<ref>{{ | + | '''Mauveine''', also known as '''[[aniline]] [[purple]]''' and '''Perkin's mauve''', was the first synthetic [[organic chemistry|organic]] [[dye]].<ref>{{citation | title = History – 150 Years of mauveine | last = Hubner | first = K. | journal = Chemie in unserer Zeit | year = 2006 | volume = 40 | issue = 4 | pages = 274–75 | doi = 10.1002/ciuz.200690054}}.</ref><ref>{{citation | title = Perkin’s Mauve: Ancestor of the Organic Chemical Industry | first = Anthony S. | last = Travis | journal = Technol. Cult. | year = 1990 | volume = 31 | issue = 1 | pages = 51–82 | doi = 10.2307/3105760}}.</ref> |
| − | | title = History | ||
| − | | | ||
| − | | journal = Chemie in unserer Zeit | ||
| − | | year = 2006 | ||
| − | | volume = 40 | ||
| − | | issue = 4 | ||
| − | | pages = | ||
| − | | doi = 10.1002/ciuz.200690054 }}</ref><ref>{{ | ||
| − | | title = Perkin’s Mauve: Ancestor of the Organic Chemical Industry | ||
| − | | | ||
| − | | journal = | ||
| − | | year = 1990 | ||
| − | | volume = 31 | ||
| − | | issue = | ||
| − | | pages = 51–82 | ||
| − | |||
| − | | doi = 10.2307/3105760 | ||
| − | }}</ref> | ||
Its chemical name is | Its chemical name is | ||
| − | 3-amino-2,±9-dimethyl-5-phenyl-7-(p-tolylamino)phenazinium acetate. The formula is C<sub>26</sub>H<sub>23</sub>N<sub>4</sub><sup>+</sup>X<sup>−</sup> (mauveine A) and C<sub>27</sub>H<sub>25</sub>N<sub>4</sub><sup>+</sup>X<sup>−</sup> (mauveine B, see below). | + | 3-amino-2,±9-dimethyl-5-phenyl-7-(p-tolylamino)phenazinium acetate. The formula is C<sub>26</sub>H<sub>23</sub>N<sub>4</sub><sup>+</sup>X<sup>−</sup> ([[mauveine A]]) and C<sub>27</sub>H<sub>25</sub>N<sub>4</sub><sup>+</sup>X<sup>−</sup> ([[mauveine B]], see below). |
{{TOCnestright}} | {{TOCnestright}} | ||
==History== | ==History== | ||
| − | Mauveine was discovered serendipitously in 1856 by 18-year old [[ | + | Mauveine was discovered serendipitously in 1856 by 18-year old [[William Henry Perkin]], who was trying to [[quinine total synthesis|synthesize]] the [[antimalarial]] drug [[quinine]] as a challenge from his professor, [[August Wilhelm von Hofmann]]. In one of his attempts, Perkin [[oxidation|oxidized]] [[aniline]] using [[potassium dichromate]]. Under these conditions, the aniline reacted with [[toluidine]] impurities in it to produce a black solid, a fairly common result in "failed" organic syntheses. While trying to clean out his flask, Perkin discovered that some component of the black solid dissolved in alcohol to give a purple-colored solution, which proved to be an effective dye for [[silk]] and other [[textile]]s. |
| − | Perkin [[patent]]ed the new dye and the following year he opened a dyeworks at [[Greenford]] on the banks<ref>Google Earth location: [http://www.ch.ic.ac.uk/motm/perkin/mauveine.kml Download]</ref> of the | + | Perkin [[patent]]ed the new dye and the following year he opened a dyeworks at [[Greenford]] on the banks<ref>Google Earth location: [http://www.ch.ic.ac.uk/motm/perkin/mauveine.kml Download]</ref> of the [[Grand Union Canal]] in [[London]] to mass produce it. It was originally manufactured under the name of ''aniline purple'' or ''[[Tyrian purple]]'', also the name of an ancient [[mollusc]]-derived natural dye.<ref name="matthew2004">{{citation | last1 = Matthew | first1 = H. C. G. | first2 = Brian Howard | last2 = Harrison | title = Oxford Dictionary of National Biography | publisher = Oxford University Press | location = Oxford | year = 2004 | isbn = 0198613938}}</ref> The name ''mauve'' was given to it in England in early 1859, from the French name for the [[mallow]] flower, and chemists later called it mauveine.<ref name="matthew2004" /> [[Mauve]] became highly fashionable in 1862 when Queen [[Victoria of the United Kingdom]] appeared at the [[Royal Exhibition]] in a mauve silk gown. Mauve fell out of [[fashion]] in the late 1860s to newer synthetic colors, but not before making Perkin's fortune and birthing the synthetic [[chemical industry]]. The U.S. National Association of Confectioners included ''mauvein'' among permitted food colorings as of the early 20th century, with a variety of equivalent names: rosolan, violet paste, chrome violet, anilin violet, anilin purple, Perkins violet, indisin, phenamin, purpurin, tyralin, Tyrian purple, and lydin.<ref>{{citation | last1 = Leffmann | first1 = Henry | first2 = William | last2 = Beam | title = Select Methods in Food Analysis | publisher = P. Blakiston's Son & Co. | location = Philadelphia | year = 1901 | url = http://books.google.com/books?id=oXI3AAAAMAAJ&pg=PA77&dq=perkins+tyrian.purple#PPA75,M1}}</ref> Later work on chemical dyes also led to the (accidental) development of modern [[chemotherapy]] (see [[Sulfonamide (medicine)|Sulfonamide]]). |
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The color of this dye may be familiar due to its widespread use in [[spirit duplicator]] (trade name Ditto) printing machines, popular during the mid-20th century. | The color of this dye may be familiar due to its widespread use in [[spirit duplicator]] (trade name Ditto) printing machines, popular during the mid-20th century. | ||
==Chemical analysis== | ==Chemical analysis== | ||
| − | A modern-day laboratory procedure for the [[organic synthesis]] of mauveine consists of dissolving a mixture of [[aniline]], [[p-toluidine]] and [[o-toluidine]] in [[sulfuric acid]] and water (large excess poor solubility) in roughly a 1:1:2 ratio followed by addition of [[potassium dichromate]] <ref> | + | A modern-day laboratory procedure for the [[organic synthesis]] of mauveine consists of dissolving a mixture of [[aniline]], [[p-toluidine]] and [[o-toluidine]] in [[sulfuric acid]] and water (large excess poor solubility) in roughly a 1:1:2 ratio followed by addition of [[potassium dichromate]].<ref>{{citation | title = A Microscale Synthesis of Mauve | last1 = Scaccia | first1 = Rhonda L. | last2 = Coughlin | first2 = David | last3 = Ball | first3 = David W. | journal = J. Chem. Educ. | year = 1998 | volume = 75 | pages = 769}}. [http://www.jce.divched.org/Journal/Issues/1998/Jun/abs769_2.html Abstract]</ref> The actual molecular structure of mauveine proved difficult to determine and was not known with certainty until 1994.<ref>{{citation | first1 = O. | last1 = Meth-Cohn | first2 = M. | last2 = Smith | title = What did W. H. Perkin actually make when he oxidised aniline to obtain mauveine? | journal = J. Chem. Soc. Perkin 1 | year = 1994 | pages = 5–7 | doi = 10.1039/P19940000005}}.</ref> |
| − | The actual molecular structure of mauveine proved difficult to determine and was not known with certainty until 1994.<ref>O. Meth-Cohn | ||
<center><gallery> | <center><gallery> | ||
| − | Image:Mauveine_a_skeletal_org.jpg|<center>[[ | + | Image:Mauveine_a_skeletal_org.jpg|<center>Skeletal formula of [[mauveine A]]</center> |
| − | Image:Mauveine_b_skeletal_org.jpg|<center>[[ | + | Image:Mauveine_b_skeletal_org.jpg|<center>Skeletal formula of [[mauveine B]]</center> |
| − | Image:Mauveine_b2_skeletal_org.jpg|<center>[[ | + | Image:Mauveine_b2_skeletal_org.jpg|<center>Skeletal formula of [[mauveine B2]]</center> |
| − | Image:Mauveine_c_skeletal_org.jpg|<center>[[ | + | Image:Mauveine_c_skeletal_org.jpg|<center>Skeletal formula of [[mauveine C]]</center> |
</gallery> | </gallery> | ||
</center> | </center> | ||
| − | It is actually a mixture of four related [[aromaticity|aromatic]] compounds, which differ only in the number and placement of [[methyl]] groups. A is built up from 2 molecules of [[aniline]], one of [[p-toluidine]] and one of [[o-toluidine]] whereas B incorporates aniline, p-toluidine and o-toluidine one molecule each. As Perkin showed in 1879,<ref> | + | It is actually a mixture of four related [[aromaticity|aromatic]] compounds, which differ only in the number and placement of [[methyl]] groups. [[Mauveine A]] is built up from 2 molecules of [[aniline]], one of [[p-toluidine]] and one of [[o-toluidine]] whereas [[Mauveine B]] incorporates aniline, p-toluidine and o-toluidine one molecule each. As Perkin showed in 1879,<ref>{{citation | authorlink = William Henry Perkin | first = W. H. | last = Perkin | title = On mauveine and allied colouring matters | journal = J. Chem. Soc., Trans. | year = 1879 | pages = 717–32 | doi = 10.1039/CT8793500717}}.</ref> mauveine B is related to the [[safranine]]s by [[oxidation|oxidative]]/[[Redox|reductive]] loss of the p-tolyl group. In fact, [[safranine]] itself is a 2,8-dimethyl [[phenazine|phenazinium]] salt, whereas the [[parasafranine]] produced by Perkin must be presumed<ref>{{citation | url = http://www.ch.ic.ac.uk/motm/perkin.html}}.</ref> to be the 1,8-(or 2,9) dimethyl [[isomer]]. |
[[Image:Rees1.jpg|thumb|right|The late Professor [[Charles Rees]] wearing a bow tie dyed with an original sample of mauveine, and holding the [[Royal Society of Chemistry|RSC]] journal named after Perkin]] | [[Image:Rees1.jpg|thumb|right|The late Professor [[Charles Rees]] wearing a bow tie dyed with an original sample of mauveine, and holding the [[Royal Society of Chemistry|RSC]] journal named after Perkin]] | ||
| − | In 2007 two other mauveine components were isolated and identified, called | + | In 2007, two other mauveine components were isolated and identified, called [[mauveine C]] (an additional p-methyl group on mauveine A) and [[mauveine B2]] (an [[isomer]] of mauveine B with methyl on different aryl group). <ref>{{citation | title = Revisiting Perkin's dye(s): the spectroscopy and photophysics of two new mauveine compounds (B2 and C) | first1 = J. | last1 = Seixas de Melo | first2 = S. | last2 = Takato | first3 = M. | last3 = Sousa | first4 = M. J. | last4 = Melo | first5 = A. J. | last5 = Parola | journal = Chem. Commun. | year = 2007 | pages = 2624–26 | doi = 10.1039/b618926a}}.</ref> |
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| + | ==References== | ||
| + | {{reflist}} | ||
==External links== | ==External links== | ||
* [http://www.rsc.org/Chemsoc/Activities/Perkin/index.asp Perkin anniversary website] | * [http://www.rsc.org/Chemsoc/Activities/Perkin/index.asp Perkin anniversary website] | ||
| − | * | + | * [http://www.ch.ic.ac.uk/motm/perkin.html Rotatable 3D models of mauveine] |
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[[Category:Azin dyes]] | [[Category:Azin dyes]] | ||
Revision as of 06:21, 24 August 2009
Mauveine, also known as aniline purple and Perkin's mauve, was the first synthetic organic dye.[1][2] Its chemical name is 3-amino-2,±9-dimethyl-5-phenyl-7-(p-tolylamino)phenazinium acetate. The formula is C26H23N4+X− (mauveine A) and C27H25N4+X− (mauveine B, see below). Template:TOCnestright
History
Mauveine was discovered serendipitously in 1856 by 18-year old William Henry Perkin, who was trying to synthesize the antimalarial drug quinine as a challenge from his professor, August Wilhelm von Hofmann. In one of his attempts, Perkin oxidized aniline using potassium dichromate. Under these conditions, the aniline reacted with toluidine impurities in it to produce a black solid, a fairly common result in "failed" organic syntheses. While trying to clean out his flask, Perkin discovered that some component of the black solid dissolved in alcohol to give a purple-colored solution, which proved to be an effective dye for silk and other textiles.
Perkin patented the new dye and the following year he opened a dyeworks at Greenford on the banks[3] of the Grand Union Canal in London to mass produce it. It was originally manufactured under the name of aniline purple or Tyrian purple, also the name of an ancient mollusc-derived natural dye.[4] The name mauve was given to it in England in early 1859, from the French name for the mallow flower, and chemists later called it mauveine.[4] Mauve became highly fashionable in 1862 when Queen Victoria of the United Kingdom appeared at the Royal Exhibition in a mauve silk gown. Mauve fell out of fashion in the late 1860s to newer synthetic colors, but not before making Perkin's fortune and birthing the synthetic chemical industry. The U.S. National Association of Confectioners included mauvein among permitted food colorings as of the early 20th century, with a variety of equivalent names: rosolan, violet paste, chrome violet, anilin violet, anilin purple, Perkins violet, indisin, phenamin, purpurin, tyralin, Tyrian purple, and lydin.[5] Later work on chemical dyes also led to the (accidental) development of modern chemotherapy (see Sulfonamide).
The color of this dye may be familiar due to its widespread use in spirit duplicator (trade name Ditto) printing machines, popular during the mid-20th century.
Chemical analysis
A modern-day laboratory procedure for the organic synthesis of mauveine consists of dissolving a mixture of aniline, p-toluidine and o-toluidine in sulfuric acid and water (large excess poor solubility) in roughly a 1:1:2 ratio followed by addition of potassium dichromate.[6] The actual molecular structure of mauveine proved difficult to determine and was not known with certainty until 1994.[7]
Skeletal formula of mauveine A 
Skeletal formula of mauveine B 
Skeletal formula of mauveine B2 
Skeletal formula of mauveine C
It is actually a mixture of four related aromatic compounds, which differ only in the number and placement of methyl groups. Mauveine A is built up from 2 molecules of aniline, one of p-toluidine and one of o-toluidine whereas Mauveine B incorporates aniline, p-toluidine and o-toluidine one molecule each. As Perkin showed in 1879,[8] mauveine B is related to the safranines by oxidative/reductive loss of the p-tolyl group. In fact, safranine itself is a 2,8-dimethyl phenazinium salt, whereas the parasafranine produced by Perkin must be presumed[9] to be the 1,8-(or 2,9) dimethyl isomer.
.jpg)
The late Professor Charles Rees wearing a bow tie dyed with an original sample of mauveine, and holding the RSC journal named after Perkin
In 2007, two other mauveine components were isolated and identified, called mauveine C (an additional p-methyl group on mauveine A) and mauveine B2 (an isomer of mauveine B with methyl on different aryl group). [10]
References
- ↑ Hubner, K. History – 150 Years of mauveine. Chemie in unserer Zeit 2006, 40 (4), 274–75. DOI: 10.1002/ciuz.200690054.
- ↑ Travis, Anthony S. Perkin’s Mauve: Ancestor of the Organic Chemical Industry. Technol. Cult. 1990, 31 (1), 51–82. DOI: 10.2307/3105760.
- ↑ Google Earth location: Download
- ↑ 4.0 4.1 Matthew, H. C. G.; Harrison, Brian Howard Oxford Dictionary of National Biography; Oxford University Press: Oxford, 2004. ISBN 0198613938
- ↑ Leffmann, Henry; Beam, William Select Methods in Food Analysis; P. Blakiston's Son & Co.: Philadelphia, 1901, <http://books.google.com/books?id=oXI3AAAAMAAJ&pg=PA77&dq=perkins+tyrian.purple#PPA75,M1>
- ↑ Scaccia, Rhonda L.; Coughlin, David; Ball, David W. A Microscale Synthesis of Mauve. J. Chem. Educ. 1998, 75, 769. Abstract
- ↑ Meth-Cohn, O.; Smith, M. What did W. H. Perkin actually make when he oxidised aniline to obtain mauveine?. J. Chem. Soc. Perkin 1 1994, 5–7. DOI: 10.1039/P19940000005.
- ↑ Perkin, W. H. On mauveine and allied colouring matters. J. Chem. Soc., Trans. 1879, 717–32. DOI: 10.1039/CT8793500717.
- ↑ , <http://www.ch.ic.ac.uk/motm/perkin.html>.
- ↑ Seixas de Melo, J.; Takato, S.; Sousa, M.; Melo, M. J.; Parola, A. J. Revisiting Perkin's dye(s): the spectroscopy and photophysics of two new mauveine compounds (B2 and C). Chem. Commun. 2007, 2624–26. DOI: 10.1039/b618926a.
External links
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